CN105669946B - A kind of preparation method of polyether-modified HMDI water-based polyurethane curing agents - Google Patents
A kind of preparation method of polyether-modified HMDI water-based polyurethane curing agents Download PDFInfo
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- CN105669946B CN105669946B CN201410657824.6A CN201410657824A CN105669946B CN 105669946 B CN105669946 B CN 105669946B CN 201410657824 A CN201410657824 A CN 201410657824A CN 105669946 B CN105669946 B CN 105669946B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
Abstract
The present invention relates to a kind of preparation method of polyether-modified HMDI water-based polyurethane curing agents, mainly by hydrogenated diphenyl methane diisocyanate H6MDI or H12MDI, polyether polyol, atent solvent and polymerization inhibitor composition；A kind of polyether-modified HMDI water-based polyurethane curing agents produced by the present invention, aromatic-free, without gylcol ether, without alkyl phenol, have the characteristics that environmental protection, scratch resistance is good, the transparency is good, chemicals-resistant is excellent, stain resistance is strong, resistance to yellowing good；There is high rigidity, high transparency with the polyurethane paint that water-based hydroxyl component is prepared, paint film scratch resistance is good, good leveling property, the features such as richness is high, intermiscibility is good, is widely used in the special curing agents such as the various bi-component waterborne Polyester Paints such as aqueous woodware paint, water-based industrial paint, aqueous plastic paint, aqueous polyurethane paint, water-base epoxy paint, Water-borne alkyd coating, aqueous polyurethane glue.
Description
Technical field
Preparation method more particularly to a kind of polyether-modified HMDI water the present invention relates to a kind of water-based polyurethane curing agent
Property polyurethane curing agent.
Background technology
The problem of China's reform is over 30 years, environmental degradation gradually display.By environment department and expert
Textual criticism, vehicle exhaust, also have the primary pollution sources such as airborne dust at VOC, are the main reason for causing haze weather, in primary pollution source
In, the VOC emission amount of coating and paint industry accounts for more than the 1/4 of VOC total releases；Chinese VOC annual emissions are more than 2000
Ten thousand tons, be 2 times, 3 times of European Union of the U.S..Haze, development of the whole society for green production, green product are fallen over a large area in the whole nation in the recent period
Especially pay attention to, government also puts into effect these industries one of quite stringent regulation, representative as green product, water paint
It is following developing direction, is to enjoy popular confidence；Recent water paint industry starts recovery actively, shows a piece of " Spring is very much in the air " scape
As.
Most representative waterborne two-component polyurethane coating in water paint, it is free of or containing minimal amount of organic molten
Agent, grain size are less than 0.1nm, have preferable dispersion stabilization, not only remain traditional solvent borne polyurethane coating some
Excellent performance, but also with film-forming temperature is low, strong adhesive force, wearability is good, hardness is big and chemicals-resistant, good weatherability etc.
Superior function is widely used as industrial protection, wood furniture, glassware, digital product and car paint.The poly- ammonia of aqueous dual-component
The low VOC content of the high-performance of two part solvent type polyurethane coating and water paint is combined by ester paint, becomes coating work
The research hotspot of industry.Aqueous polyurethane coating with bi component is aqueous polyalcohol by containing (- OH) base and low viscous containing (- NCO) base
Polyisocyanate curing agent composition is spent, film performance mainly forms what is determined with structure and curing agent by hydroxy resin.
At present, common polyurethane curing agent is mostly solvent type in the market, and water-based polyurethane curing agent is substantially
Offshore company is expensive such as productions such as Bayer, Rhodia, of high cost, is the main reason for water paint is difficult to promote, opens
The water-based polyurethane curing agent of hair production domesticization low cost becomes the first choice of domestic coating industry.
Invention content
The present invention is intended to provide a kind of preparation method of polyether-modified HMDI water-based polyurethane curing agents.
In order to solve the problems, such as techniques as described above, the present invention takes following technical scheme：The present invention relates to a kind of polyethers
The preparation method of modified HMDI water-based polyurethane curing agents, including following components：HMDI hydrogenated diphenyl methane diisocyanates
60~80%, polyether polyol 8~20%, atent solvent 10~25%, polymerization inhibitor 2,4,6- tri- (dimethylamino methyl) phenol
0.1~0.5%；The hydrogenated diphenyl methane diisocyanate is H6MDI or H12MDI；The polyether polyol requirement
It is not aqueous, select the polyethylene glycol of Mr 600~1000, the poly glycol monomethyl ether of Mr 600~1000, Mr 600~1000
A kind of or combination of polyethylene glycol monobutyl ether；The atent solvent requirement is not aqueous, selection diethylene glycol ether acetate,
Propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetate, dipropylene glycol methyl ether acetate a kind of or combination.
The present invention proposes a kind of preparation method of polyether-modified HMDI water-based polyurethane curing agents, and preparation process is as follows：
It is added in kettle is added dropwise and measures polyether polyol, after carrying out heating in vacuum dehydration 2h, be passed through N2It seals spare；In synthesis reactor
In, by formula ratio addition atent solvent and after carrying out heating in vacuum dehydration 2h, it is passed through N2, hydrogenated diphenyl first is added in by formula ratio
After alkane diisocyanate dissolves by heating, polyether polyol is added in a manner of being added dropwise, 3~4hr of isothermal reaction is kept at 70~80 DEG C,
Start to sample after reaction 2h, it is later primary every 0.5h samplings, NCO content is detected, resistance is added in when NCO content is close to theoretical value
Poly- 2,4,6- tri- (dimethylamino methyl) phenol 0.1~0.5% of agent, cold filtration obtain a kind of solid content 70~80%, NCO
Content is 12.0~18.0% polyether-modified HMDI water-based polyurethane curing agents.
Polyether-modified HMDI water-based polyurethane curing agents produced by the present invention, aromatic-free, without gylcol ether, be free of
Alkyl phenol；Have the characteristics that environmental protection, scratch resistance is good, the transparency is good, chemicals-resistant is excellent, stain resistance is strong, resistance to yellowing good.With water
Property the polyurethane paint prepared of hydroxy component there is high rigidity, high transparency, paint film scratch resistance is good, good leveling property, and richness is high, phase
The features such as dissolubility is good is for various bi-component waterborne Polyester Paints, water such as aqueous woodware paint, water-based industrial paint, aqueous plastic paints
The special curing agents such as property polyurethane paint, water-base epoxy paint, Water-borne alkyd coating, aqueous polyurethane glue.
Specific embodiment
Embodiment 1：
It is added in kettle is added dropwise and measures 11 parts of polyethylene glycol monobutyl ethers (Mr 1000), after carrying out heating in vacuum dehydration 2h,
It is passed through N2It seals spare；In synthesis reactor, add in 20 parts of propylene glycol methyl ether acetates, and carry out heating in vacuum dehydration 2h after, lead to
Enter N2, add in 69 parts of H12After MDI is dissolved by heating, polyethylene glycol monobutyl ether is added in a manner of being added dropwise, constant temperature is kept at 75~80 DEG C
3~4hr is reacted, 2,4,6- tri- 0.2 part of (dimethylamino methyl) phenol, cold filtration are added in when NCO content is close to calculated value
Obtain a kind of solid content 80%, the polyether-modified H that NCO content is 17.2%12MDI water-based polyurethane curing agents.
Embodiment 2：
It is added in kettle is added dropwise and measures 8 parts of polyethylene glycol monobutyl ethers (Mr 1000), after carrying out heating in vacuum dehydration 2h,
It is passed through N2It seals spare；In synthesis reactor, after adding in 20 parts of propylene glycol methyl ether acetates and carrying out heating in vacuum dehydration 2h, it is passed through
N2, add in 72 parts of H6After MDI is dissolved by heating, polyethylene glycol monobutyl ether is added in a manner of being added dropwise, isothermal reaction is kept at 70~80 DEG C
3~4hr, 2,4,6- tri- 0.2 part of (dimethylamino methyl) phenol are added in when NCO content is close to calculated value, and cold filtration is made
Obtain a kind of solid content 80%, the polyether-modified H that NCO content is 17.6%6MDI water-based polyurethane curing agents.
Embodiment 3：
It is added in kettle is added dropwise and measures 10 parts of polyethylene glycol (Mr 1000), after carrying out heating in vacuum dehydration 2h, be passed through N2
It seals spare；In synthesis reactor, after adding in 20 parts of diethylene glycol ether acetates and carrying out heating in vacuum dehydration 2h, it is passed through N2,
Add in 70 parts of H12After MDI is dissolved by heating, polyethylene glycol monobutyl ether is added in a manner of being added dropwise, isothermal reaction 3 is kept at 75~80 DEG C
~4hr adds in 2,4,6- tri- 0.2 part of (dimethylamino methyl) phenol when NCO content is close to calculated value, and cold filtration obtains
A kind of solid content 80%, the polyether-modified H that NCO content is 16.4%12MDI water-based polyurethane curing agents.
Embodiment 4：
Polyether-modified H in above-described embodiment 1,2,312MDI aqueous polyurethanes are used to prepare bi-component water as second component
The first component formula of property woodenware polyurethane lacquer is as follows：Water-based hydroxyl-dispersions of polyurethanes 85, ground wetting agent 0.2, levelling agent
0.2nd, antifoaming agent 0.2, thickener 0.5, preservative 0.2, coalescents 3.0, PH conditioning agents 0.2, water 10.5；First component:Second group
Divide=100:12~18.
The performance of bi-component waterborne woodenware polyurethane lacquer is used for the polyether-modified HMDI aqueous polyurethanes of the present invention, is pressed
It is detected according to relevant national standard, test result is as shown in table 1.
1 bi-component waterborne woodenware polyurethane lacquer the performance test results of table
Although the present invention has described it in detail and cited embodiments, it but for those of ordinary skill in the art, shows
Various schemes, modification and the change that can so make as specified above, should be construed as being included within the scope of the claims.
Claims (3)
1. a kind of polyether-modified HMDI water-based polyurethane curing agents, it is characterised in that：The aqueous poly- ammonia of the polyether-modified HMDI
Ester curing agent, preparation process are as follows：
A, 11 parts of polyethylene glycol monobutyl ethers are added in kettle is added dropwise, after carrying out heating in vacuum dehydration 2h, are passed through N2It seals spare；Its
In, its molecular weight of polyethylene glycol monobutyl ether Mr is 1000；
B, in synthesis reactor, 20 parts of propylene glycol methyl ether acetates are added in, after carrying out heating in vacuum dehydration 2h, are passed through N2, add in 69 parts
H12After MDI is dissolved by heating, the polyethylene glycol monobutyl ether being dehydrated in a steps is added dropwise, 3~4hr of isothermal reaction is kept at 75~80 DEG C,
2,4,6- tri- 0.2 part of (dimethylamino methyl) phenol are added in when NCO content is close to calculated value, cold filtration is made and contains
Admittedly amount 80%, NCO content are the 17.2% polyether-modified HMDI water-based polyurethane curing agents.
2. a kind of polyether-modified HMDI water-based polyurethane curing agents, it is characterised in that：The aqueous poly- ammonia of the polyether-modified HMDI
Ester curing agent, preparation process are as follows：
A, 8 parts of polyethylene glycol monobutyl ethers are added in kettle is added dropwise, after carrying out heating in vacuum dehydration 2h, are passed through N2It seals spare；Its
In, its molecular weight of polyethylene glycol monobutyl ether Mr is 1000；
B, in synthesis reactor, 20 parts of propylene glycol methyl ether acetates are added in, after carrying out heating in vacuum dehydration 2h, are passed through N2, add in 72 parts
H6After MDI is dissolved by heating, the polyethylene glycol monobutyl ether being dehydrated in a steps is added dropwise, 3~4hr of isothermal reaction is kept at 70~80 DEG C,
2,4,6- tri- 0.2 part of (dimethylamino methyl) phenol are added in when NCO content is close to calculated value, cold filtration is made and contains
Admittedly amount 80%, NCO content are the 17.6% polyether-modified HMDI water-based polyurethane curing agents.
3. a kind of polyether-modified HMDI water-based polyurethane curing agents, it is characterised in that：The aqueous poly- ammonia of the polyether-modified HMDI
Ester curing agent, preparation process are as follows：
A, 10 parts of polyethylene glycol are added in kettle is added dropwise, after carrying out heating in vacuum dehydration 2h, are passed through N2It seals spare；Wherein, it is described
Its molecular weight of polyethylene glycol Mr is 1000；
B, in synthesis reactor, 20 parts of diethylene glycol ether acetates are added in, after carrying out heating in vacuum dehydration 2h, are passed through N2, add in 70
Part H12After MDI is dissolved by heating, the polyethylene glycol being dehydrated in a steps is added dropwise, 3~4hr of isothermal reaction is kept at 75~80 DEG C, when
2,4,6- tri- 0.2 part of (dimethylamino methyl) phenol are added in when NCO content is close to calculated value, cold filtration is made containing solid
Amount 80%, the polyether-modified HMDI water-based polyurethane curing agents that NCO content is 16.4%.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410657824.6A CN105669946B (en) | 2014-11-18 | 2014-11-18 | A kind of preparation method of polyether-modified HMDI water-based polyurethane curing agents |
| PCT/CN2015/080480 WO2016078387A1 (en) | 2014-11-18 | 2015-06-01 | Method for preparing polyether-modified hmdi aqueous polyurethane curing agent |
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|---|---|---|---|
| CN201410657824.6A CN105669946B (en) | 2014-11-18 | 2014-11-18 | A kind of preparation method of polyether-modified HMDI water-based polyurethane curing agents |
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| CN105669946A CN105669946A (en) | 2016-06-15 |
| CN105669946B true CN105669946B (en) | 2018-06-12 |
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| WO (1) | WO2016078387A1 (en) |
Families Citing this family (11)
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| CN107163663A (en) * | 2017-07-13 | 2017-09-15 | 合肥市龙阳节能新材料有限公司 | A kind of preparation method of the aqueous repairing paste putty of woodcare paint |
| CN109609005A (en) * | 2018-10-31 | 2019-04-12 | 安徽开林新材料股份有限公司 | A kind of dual-component aqueous polyurethane woodwork coating |
| CN109553754A (en) * | 2018-11-28 | 2019-04-02 | 韶关市合众化工有限公司 | A kind of polyarylsulfone (PAS) modified polyurethane curing agent that high rigidity solvent resistance is good |
| CN110078888B (en) * | 2019-04-04 | 2020-07-28 | 华南理工大学 | Porous organic polymer connected by thiourea structure and preparation method and application thereof |
| CN110894293A (en) * | 2019-12-06 | 2020-03-20 | 合众（佛山）化工有限公司 | Preparation method of fluorinated polyimide modified HMDI waterborne polyurethane curing agent |
| CN111019078B (en) * | 2019-12-31 | 2022-04-05 | 北京华腾新材料股份有限公司 | Waterborne polyurethane curing agent and preparation method and application thereof |
| CN111454414B (en) * | 2020-05-15 | 2022-07-12 | 万华化学集团股份有限公司 | Matte polyisocyanate curing agent and preparation method and application thereof |
| CN113024767B (en) * | 2021-03-04 | 2022-04-29 | 浙江恒达新材料股份有限公司 | Cationic waterborne polyurethane emulsion and preparation method and application thereof |
| CN113105489B (en) * | 2021-03-31 | 2022-06-14 | 华南理工大学 | Hydroxyl carborane derivative containing ether bond, modified curing agent, and preparation method and application thereof |
| CN113604143B (en) * | 2021-08-04 | 2022-07-22 | 佛山市精信汇明科技有限公司 | Two-component waterborne polyurethane scratch-resistant wear-resistant PVC (polyvinyl chloride) coating and preparation method thereof |
| CN114395109B (en) * | 2022-01-19 | 2023-06-06 | 上海稻畑精细化工有限公司 | Waterborne polyurethane curing agent and preparation method thereof |
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| CN105669946A (en) | 2016-06-15 |
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